Reaction equation
[C:1]([CH:4]1[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[F:7][C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1.O.C(OCC)(=O)C>C(OCC)C.O1CCCC1>[CH:4]1([C:1]([C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)([OH:3])[CH3:2])[CH2:6][CH2:5]1Participants
7
Conditions
- Temperature
- 0 °C
Procedure
0.50 g (5.94 mmol) of acetylcyclopropane was dissolved at 0° C. in 5 ml of diethyl ether, and 8.9 ml (8.91 mmol) of a 1N solution of 4-fluorophenylmagnesium bromide in tetrahydrofuran were slowly added dropwise. Stirring at 0° C. for 1 h was followed by warming to RT, and the reaction solution was mixed with water and ethyl acetate, and the phases were separated. The organic phase was washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvents were removed in vacuo. The crude product was purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10/1) to result in 0.99 g (93% of theory) of the title compound.
Workup
- temperatureby warming to RT
- customthe phases were separated
- washThe organic phase was washed with saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- customthe solvents were removed in vacuo
- customThe crude product was purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10/1)
Sources & evidence
- ORD record
- ord-29ddf9cdef3b4eae9fb2f2c1499a76cc
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063234B2
Linked notes
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